Winding Cypress Real Estate

Welcome to Winding Cypress, a stunning new development nestled in the heart of Naples, Florida, within beautiful Collier County. This vibrant community is designed for those who seek a perfect blend of luxury, comfort, and an active lifestyle, all while being surrounded by the breathtaking natural beauty that Naples is renowned for.

Winding Cypress features an array of meticulously crafted single-family homes, each offering modern designs and high-end finishes. With spacious floor plans and customizable options, residents can create their dream sanctuary tailored to their unique tastes. The community embraces a sense of connection, featuring lush landscapes, serene lakes, and winding paths that invite leisurely strolls and outdoor adventures.

At Winding Cypress, the amenities are truly exceptional. Residents can enjoy a state-of-the-art clubhouse, a resort-style pool, fitness center, and a lively social calendar that fosters community engagement. Whether you’re looking to unwind by the pool, stay active with fitness classes, or join in on neighborhood events, there’s something for everyone.

Situated just minutes from Naples’ pristine beaches, world-class dining, and upscale shopping, Winding Cypress offers the perfect location for those who appreciate the finer things in life. Explore the vibrant arts scene, indulge in gourmet cuisine, or simply bask in the sun on the sandy shores – the possibilities are endless.

Discover the charm of Winding Cypress, where luxury living meets the natural splendor of Florida’s Gulf Coast. Your dream home awaits in this idyllic community, ready to welcome you to a lifestyle of comfort, convenience, and connection.

Newest Listings in Winding Cypress

7230 Live Oak Drive, Naples $1,195,000

Beautiful home inside and out Pinnacle style home in Winding Cypress. This home features 3 generous size bedrooms, 3 full bath , 2 car plus golf cart garage . Custom ov...

3 Beds
3 Baths
Winding Cypress SubDv.

6825 Greenbriar Court, Naples $965,000

Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor livi...

4 Beds
3 Baths
Winding Cypress SubDv.

7564 Winding Cypress Drive, Naples image

7564 Winding Cypress Drive, Naples $1,060,000

Most lake lots give you water. This one gives you the sunset. The western exposure at 7564 Winding Cypress Drive turns the back of the house into the best seat in the com...

4 Beds
2 Baths
Winding Cypress SubDv.

7700 Winding Cypress Drive, Naples image

7700 Winding Cypress Drive, Naples $1,250,000

BEAUTIFUL AND METICULOUSLY MAINTAINED 5 BEDROOM, 3 BATH HOME IN DIVOSTA’S GATED WINDING CYPRESS COMMUNITY, ONE OF NAPLES MOST DESIRABLE LOCATIONS, CONVENIENT TO DOWNTOWN ...

5 Beds
3 Baths
Winding Cypress SubDv.

6907 Cocoplum Street, Naples $1,295,000

PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with pea...

3 Beds
3 Baths
Winding Cypress SubDv.

7759 Winding Cypress Drive, Naples image

7759 Winding Cypress Drive, Naples $1,300,000 ▼

PRICE IMPROVEMENT _Ready for New Owners- Look at all the upgrades in this prestigious, stately, and expansive Stonewater offering everything option possible located in th...

4 Beds
5 Baths
Winding Cypress SubDv.

7156 Live Oak Drive, Naples $599,900

This TURNKEY FURNISHED TRUE 3-BEDROOM , 2-bathroom villa offers the ultimate blend of luxury, comfort, and effortless living is move-in ready for your immediate enjoymen...

3 Beds
2 Baths
Winding Cypress SubDv.

6727 Pennyroyal Drive, Naples $920,000 ▼

This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious cor...

3 Beds
2 Baths
Winding Cypress SubDv.

7478 Winding Cypress Drive, Naples image

7478 Winding Cypress Drive, Naples $1,349,500

BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, ...

3 Beds
3 Baths
Winding Cypress SubDv.

7666 Jacaranda Lane, Naples $575,000

Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath...